Last October we took a family trip to Kennebunkport, Maine with our two young kids. Our son was two years old and our daughter was ten months old, and it ended up being one of our favorite fall trips as a family of four.
We arrived on October 17th, just as the fall foliage was reaching its peak. The trees around town were full of color, the air was crisp, and the harbor was lined with boats gently docked along the water. It felt like stepping into a classic New England coastal postcard.
With its walkable town, beautiful coastal views, and relaxed pace, Kennebunkport turned out to be the perfect place for a fall trip with young kids.
Where We Stayed: The Nonantum Resort
For most of our stay in Kennebunkport we chose the Nonantum Resort
https://www.nonantumresort.com/
It turned out to be the perfect hotel for a trip with young kids.
The property sits right along the water and immediately feels welcoming and relaxed. What really made it special for our family was the open lawn in the backyard and the small lighthouse on the property. For our son it felt larger than life — a place where he could run around and explore while we enjoyed the harbor views.
Another thing we loved about the Nonantum was how incredibly family friendly it felt. Traveling with a two-year-old and a ten-month-old means simple things make a big difference, and the resort made everything easy.
Each morning started with a breakfast buffet included with the stay, which was a great way to begin the day with kids.
One of the more unique experiences during our stay was the floating sauna overlooking the harbor, which was a relaxing way to start the morning before getting the kids ready and heading into town.
The Nonantum is also within easy walking distance of Kennebunkport’s shops and restaurants, which made exploring the town simple with kids.
One Night at The Colony Hotel
Before heading home we extended our trip by one night and stayed at The Colony Hotel
https://www.thecolonyhotel.com/
The Colony felt like stepping straight out of an old movie.
The hotel sits right along the ocean and has the kind of timeless New England charm that is hard to describe until you see it in person. The long porches, classic architecture, and ocean views make it feel like a place where families have been vacationing for generations.
During our stay our son loved playing putt-putt golf on the property, which ended up being one of his favorite moments of the trip.
Even though we were only there for one night, it was a memorable way to end our time in Kennebunkport.
Things We Loved Doing in Kennebunkport with Kids
One of the highlights of the trip was visiting Brackett’s Orchard
https://www.brackettorchard.com/
The orchard was beautiful and perfect for exploring with young kids.
We pulled our daughter through the orchard in a wagon while our son ran around picking apples. It ended up being one of those simple family moments that perfectly captured fall in New England.
The kids also loved riding the train through the orchard, which made the experience even more fun.
Back at the Nonantum Resort we spent time playing on the open lawns surrounded by fall leaves. Watching the kids run around in the crisp fall air ended up being one of our favorite parts of the trip.
The resort also hosted evening s’mores, which quickly became a fun nightly tradition.
A Day Trip to Portland
Since Portland is only about a 40-minute drive from Kennebunkport, we spent a day exploring the city.
One of the most famous stops in the area is Portland Head Light
https://www.portlandheadlight.com/
It’s one of the most photographed lighthouses in the country and sits along a beautiful stretch of coastline.
Because the weather can be unpredictable in the fall, we also spent time at the Portland Children’s Museum & Theatre of Maine
https://www.kitetails.org/
It ended up being the perfect rainy-day activity for the kids.
Beach Walks and Fall Sunsets
Another simple favorite was walking along the beach. Even though it was chilly, the coastal walks were beautiful and the kids loved exploring the sand and watching the waves.
Watching the sunset over the ocean ended up being one of the most peaceful moments of the entire trip.
The Seashore Trolley Museum
We also visited the Seashore Trolley Museum
https://trolleymuseum.org/
It’s one of the largest electric railway museums in the world, and we rode a trolley out to pick pumpkins. It was a really fun fall activity and something a little different that the kids really enjoyed.
Restaurants We Loved in Kennebunkport
Kennebunkport ended up being just as enjoyable for dining as it was for exploring.
One of our favorite dinners was at Port Fish & Chop House
https://portfishandchophouse.com/
The restaurant overlooks the water and the sunset views while we were eating made it a really memorable meal.
We also loved The Boathouse
https://boathouseme.com/
It was the perfect place to grab a classic Maine lobster roll right along the harbor.
Another fun stop was Batson River Brewing & Distilling
https://batsonriver.com/
We also enjoyed dinner at The Lost Fire
https://thelostfire.com/
And for a relaxed stop we visited Wandby Landing
https://wandbylanding.com/
Wandby Landing has a beautiful marsh view, which made it a great place to slow down and enjoy the coastal scenery.
What the Kids Wore for Fall in Kennebunkport
One of our favorite parts of fall trips like this is dressing the kids for the season. The crisp air, fall foliage, and classic New England setting make the perfect backdrop for timeless children’s clothing.
For this trip both kids wore several pieces from the Beaufort Bonnet fall collection along with a few other classic children’s brands.
Our son wore a few different quarter-zip pullovers, which were perfect for layering in the cool fall weather.
Hayword Half-Zip (Carolina Hunt Club with Nantucket Red)
https://www.thebeaufortbonnetcompany.com/products/hayword-half-zip-carolina-hunt-club-with-nantucket-red
Hayword Half-Zip (Beale Street Blue Stripe)
https://www.thebeaufortbonnetcompany.com/products/hayword-half-zip-beale-street-blue-stripe-with-beale-street-blue-stork
He also wore a classic pumpkin plaid longall
https://www.lilaandhayes.com/products/harrison-boys-woven-pima-cotton-longall-pumpkin-plaid
Our daughter wore cozy fall outfits during the trip including the Sadie Sweatshirt Dress in Blue Bon Ton Bows
https://sugarplumtree.com/products/sadie-sweatshirt-dress-blue-bon-ton-bows
She also wore the Bow Crochet Sweater from Little English
https://www.littleenglish.com/products/bow-crochet-sweater
Traditional children’s clothing just seemed to fit naturally with the setting. Between the fall foliage, historic homes, and coastal scenery, Kennebunkport felt like the perfect backdrop for those classic styles.
Final Thoughts
Our fall trip to Kennebunkport ended up being the perfect mix of coastal scenery, simple family activities, and time together.
Between the welcoming atmosphere of the Nonantum Resort, apple picking at Brackett’s Orchard, sunset beach walks, and the timeless charm of The Colony Hotel, it was a trip we’ll always remember.
It’s the kind of place that feels timeless — and one we hope to return to again as our kids grow.
The Heirloom Childhood 
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